CN1221864C - Process for producing acid sensitive liquid composition containing a carbonate - Google Patents

Process for producing acid sensitive liquid composition containing a carbonate Download PDF

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Publication number
CN1221864C
CN1221864C CNB028080866A CN02808086A CN1221864C CN 1221864 C CN1221864 C CN 1221864C CN B028080866 A CNB028080866 A CN B028080866A CN 02808086 A CN02808086 A CN 02808086A CN 1221864 C CN1221864 C CN 1221864C
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filter disc
fluid composition
acid
exchange resin
ion exchange
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CN1502063A (en
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J·E·奥博兰德
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AZ Electronic Materials Japan Co Ltd
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AZ Electronic Materials Japan Co Ltd
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G03F7/30—Imagewise removal using liquid means
    • G03F7/32—Liquid compositions therefor, e.g. developers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
    • B01J20/28014—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their form
    • B01J20/2803—Sorbents comprising a binder, e.g. for forming aggregated, agglomerated or granulated products
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
    • B01J20/28002—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their physical properties
    • B01J20/28004—Sorbent size or size distribution, e.g. particle size
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
    • B01J20/28014—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their form
    • B01J20/28028—Particles immobilised within fibres or filaments
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
    • B01J20/28014—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their form
    • B01J20/28033—Membrane, sheet, cloth, pad, lamellar or mat
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
    • B01J20/28054—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J20/28078—Pore diameter
    • B01J20/28085—Pore diameter being more than 50 nm, i.e. macropores
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J47/00—Ion-exchange processes in general; Apparatus therefor
    • B01J47/018—Granulation; Incorporation of ion-exchangers in a matrix; Mixing with inert materials
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J47/00—Ion-exchange processes in general; Apparatus therefor
    • B01J47/12—Ion-exchange processes in general; Apparatus therefor characterised by the use of ion-exchange material in the form of ribbons, filaments, fibres or sheets, e.g. membranes
    • B01J47/133—Precoat filters
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/16—Coating processes; Apparatus therefor
    • G03F7/162—Coating on a rotating support, e.g. using a whirler or a spinner
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/16—Coating processes; Apparatus therefor
    • G03F7/168—Finishing the coated layer, e.g. drying, baking, soaking

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Analytical Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Nanotechnology (AREA)
  • Treatment Of Liquids With Adsorbents In General (AREA)
  • Filtering Materials (AREA)
  • Separation Using Semi-Permeable Membranes (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)

Abstract

Disclosed is a method for producing an acid sensitive liquid composition. The method involves passing an acid sensitive liquid composition contained a carbonate represented by the formula ROC(=O(OR<1> wherein R and R<1> independently are a hydrocarbyl group of 1 to about 10 carbon atoms, through at least one of the following two filter sheets: (a) a filter sheet containing a selfsupporting fibrous matrix having immobilized therein a particulate filter aid and a particulate ion exchange resin having an average particle size of from about 2 to about 10 microns, wherein the particulate filter aid and ion exchange resin particles are distributed substantially uniformly throughout a cross-section of said matrix; and/or (b) a filter sheet containing a self-supporting matrix of fibers having immobilized therein particulate filter aid and binder resin, and having an average pore size of about 0.05 to 0.5 mu mum. Also disclosed is a method for treating a film of photoresist composition disposed on a surface, which involves contacting the photoresist composition with an acid sensitive liquid composition prepared by the aforementioned method, in an amount sufficient to produce a substantially uniform film thickness of the photoresist compostion across the film surface.

Description

Production contains the method for the acid-sensitive fluid composition of carbonic ester
The field of the invention
The invention provides the method for producing the acid-sensitive fluid composition that is suitable for photo-corrosion-resisting agent composition, or the method that is used to process photo-corrosion-resisting agent composition.This method comprises by allowing acid-sensitive fluid composition remove impurity metal ion by one or more filter discs from the acid-sensitive fluid composition that contains carbonic ester.One of filter disc comprises the self-supporting fibre substrate that wherein is fixed with particle filtration aid and particle ion exchange resin.Another filter disc comprises and wherein is fixed with particle filtration aid and resin glue, but do not contain the self-supporting cellulose fiber substrate of any ion exchange resin.
Background of the present invention
Photo-corrosion-resisting agent composition is used to prepare the microlithography technology (microlithography) of miniaturized electric sub-component, as is used to make computer chip and integrated circuit.Generally, in these methods, at first the thin coating film with photo-corrosion-resisting agent composition is applied over base material, as is used to prepare the silicon wafer of integrated circuit.Then with substrates coated baking, to evaporate any solvent in the photo-corrosion-resisting agent composition and coating is fixed on the base material.Next the coating surface of the baking of base material carries out imaging (image-wise) radiant exposure.
This radiant exposure has caused the chemical conversion of coating surface exposure area.Visible light, ultraviolet ray (UV), electron beam and x-ray radiation can be the emission types that is usually used in microlithography technology at present.After this imaging exposure, the radiant exposure zone (under the situation of positive photoresist) or the unexposed area (under the situation of negative photoresist) on substrate coating surface are handled and removed to coating material with developer solution.
Metal ion pollution has become makes outstanding issue in high density integrated circuit, computer hard disc driver and the computer chip, has usually caused the defective that increases, yield losses, degraded and performance to reduce.In plasma method, metallic ion such as sodium and iron are in being present in photoresist the time, and they especially cause pollution in removing of photoresist by plasma (stripping) process.Yet these problems can significantly be overcome in this manufacture method, for example absorb (gettering) by the HCl that utilizes pollutant at high annealing in the cycle.
Because electron device is complicated day by day,, these problems are difficult to more be overcome so becoming.When silicon wafer is coated with the liquid positive photoresist and for example removes photoresist with the oxygen microwave plasma subsequently, find that usually semi-conductive performance and stability reduce, because it is believed that the very low-level metallic ion of existence.When repeating the removing of photoresist by plasma method, usually more degradeds of generating device.The main cause of having found these problems is the metal ion pollution in the photoresist, especially sodium and ferric ion.Often discovery is lower than the performance of these electron devices of metallic ion level meeting adverse effect of 100ppb (parts per billion (ppb)).Impurity level in the photo-corrosion-resisting agent composition all passed through (1) in the past and at present and selects to satisfy the raw material of photo-corrosion-resisting agent composition of strict impurity level regulation and (2) and carefully control photoresist agent prescription and machined parameters and control to avoid impurity is incorporated in the photo-corrosion-resisting agent composition.Because using, photoresist becomes advanced day by day, so must make stricter impurity regulation.
As the component of photo-corrosion-resisting agent composition or the fluid composition that is used to process photo-corrosion-resisting agent composition comprise solvent, developer, irrigation, thinning agent and edge bead remover (edgebead remover).In producing complicated semiconductor devices, seem more and more important for the fluid composition that provides each metal ion pollution level to be lower than 50ppb.The invention provides the method for producing this fluid composition with low-down concentration of metal ions.
Two types photo-corrosion-resisting agent composition is arranged, i.e. negativity and positive photoresist composition.When the negative photoresist composition being carried out the radiant image exposure, the dissolubility of zone in developer solution that is exposed to the photo-corrosion-resisting agent composition of radiation diminishes (cross-linking reaction has for example taken place), and the unexposed area of photoresist coating keeps solvable relatively to this solution.Therefore, the negative photoresist of handling exposure with developer has caused the removal and the formation of negativity image in coating of the unexposed area of photoresist coating, thereby exposes the required part on the base material basal surface of deposition photo-corrosion-resisting agent composition.
On the contrary, when the positive photoresist composition being carried out the radiant image exposure, the solubleness of those zones in developer solution that is exposed to the photo-corrosion-resisting agent composition of radiation becomes big, and unexposed those zones keep being insoluble to relatively developer solution.Therefore, the exposed positive photoresist is handled the removal of the exposure area that has caused coating and form positive images in the photoresist coating with developer.Equally, the required part of having exposed the base material basal surface.
After this development operation, the unshielded base material of part can be used processing such as base material etchant solutions or plasma gas now.Etchant solutions or plasma gas etch have wherein been removed that part of base material of photoresist coating in developing process.Wherein the substrate regions that still keeps of photoresist coating is protected, therefore, has formed etched pattern at the base material corresponding to the photomask that is used for the radiant image exposure.After, in the operating process of removing photoresist, can remove the reserve area of photoresist coating, stayed the etching substrate surface of cleaning.In some cases, need be after development step and before etching step the remaining photoresist layer of thermal treatment so that increase it to the bounding force of bottom substrate and its etch resistant solution.
At present, the positive photoresist composition more is expected than negative photoresist, because the former generally has better resolving power and pattern transfer characteristics.The photoresist resolving power be defined in exposure and development step afterwards photo-corrosion-resisting agent composition can transfer to minimal characteristic on the base material from photomask with high image edge acuity.In many production applications of today, about photoresist resolving power less than 1 micron is very common.In addition, always wish that almost the photoresist wall profile of development is almost vertical with base material.Development and this boundary between the non-developing regional in the photoresist coating are converted into the accurate patterns transfer of mask image on base material.
U.S. Patent No. 6,103,122 disclose the filter disc that comprises the self-supporting fibre substrate that wherein is fixed with particle filtration aid and particle ion exchange resin, and wherein said particle filtration aid and particle ion exchange resin are evenly distributed on the whole cross section of described matrix basically.Also disclose the method for removing ionic impurity from the photoresist agent solution in this patent, this method comprises allows the photoresist agent solution by described filter disc, to remove ionic impurity wherein.
The U.S. Patent Application Serial Number 09/693 that on October 20th, 2000 proposed, 215 disclose the edge bead remover that is used for being arranged in as film lip-deep photo-corrosion-resisting agent composition, main by the about 50 at least a carbonic acid two (C to about 80 weight portions that comprise based on solvent mixture weight 1-C 3) Arrcostab and form to the solvent mixture of the cyclopentanone of about 50 weight portions based on about 20 of solvent mixture.This application also discloses the method that is arranged in lip-deep photo-corrosion-resisting agent composition film of handling, this method comprise allow photo-corrosion-resisting agent composition with present in an amount at least sufficient to that the solvent mixture that has the photo-corrosion-resisting agent composition of basic homogeneous film thickness on whole surface is contacted, wherein solvent mixture comprises based on about 50 at least a carbonic acid two (C of about 80 weight portions of solvent mixture weight 1-C 3) Arrcostab and based on solvent mixture about 20 to the cyclopentanone of about 50 weight portions.
General introduction of the present invention
The invention provides the method for producing acid-sensitive fluid composition, said method comprising the steps of:
Allow and contain useful formula ROC (=O) OR 1The carbonic ester of expression (wherein R and R 1Independently be 1 to the alkyl of about 10 carbon atoms) at least a by following two kinds of filter discs of acid-sensitive fluid composition:
(a) comprise the filter disc of the self-supporting fibre substrate that wherein is fixed with particle filtration aid and particle ion exchange resin, described ion exchange resin has about 2 particle mean sizes to about 10 microns (μ m), and wherein said particle filtration aid and ion-exchange resin particles are evenly distributed on the whole cross section part of described matrix basically; And/or
(b) comprise the filter disc of the self-supporting fibre substrate that wherein is fixed with particle filtration aid and resin glue, described filter disc has the average pore size of about 0.0.05 to 0.5 μ m; Thereby obtain acid-sensitive fluid composition.
The present invention also provides the method for handling the film that is arranged in lip-deep photo-corrosion-resisting agent composition, described method comprises allows described photo-corrosion-resisting agent composition contact with acid-sensitive fluid composition by method for preparing, presents in an amount at least sufficient to make the described photo-corrosion-resisting agent composition that has basic homogeneous film thickness on described whole film surface.
The description of preferred embodiment
The invention provides the method for producing acid-sensitive fluid composition.A step of this method comprises allowing and contains useful formula ROC (=O) OR 1The carbonic ester of expression (wherein R and R 1Independently be 1 to about 10 carbon atoms, or the alkyl of 1-5 carbon atom) acid-sensitive fluid composition pass through at least a of following two kinds of filter discs.
Here employed term " hydrocarbyl substituent " or " alkyl " use with its common meaning, and this is known to those technician in this area.Specifically, it is meant the carbon atom with the remainder that is directly connected in this molecule and has the group that accounts for leading hydrocarbon characteristic.The example of alkyl comprises:
(1) hydrocarbon substituent, i.e. aliphatic (for example alkyl or alkenyl), alicyclic (naphthenic base for example, cycloalkenyl group) substituting group, and aromatics-, the aromatic substituent of aliphatic series-and alicyclic-replace, and the cyclic substituents (for example, two substituting groups form alicyclic group together) finished by another part of molecule of this ring wherein;
(2) hydrocarbon substituent of Qu Daiing promptly, with regard to the present invention, contains the substituting group that does not change the non-hydrocarbyl group (for example, halogen (especially chlorine and fluorine), hydroxyl, alkoxy, sulfydryl, alkyl thiol, nitro, nitroso-and sulphur oxygen base) that accounts for leading hydrocarbon substituent;
(3) assorted substituting group promptly, with regard to the present invention, accounts for leading hydrocarbon characteristic though have, and contains the substituting group of non-carbon atom in ring of being made up of carbon atom in addition or chain.Heteroatoms comprises sulphur, oxygen, nitrogen, and comprises substituting group such as pyridine radicals, furyl, thienyl and imidazole radicals.Generally, per 10 carbon atoms existence is no more than 2 in alkyl, preferably is no more than 1 non-hydrocarbon substituent; Typically, in alkyl, there is not non-hydrocarbon substituent.
In one embodiment, R and R 1Independently be methyl or ethyl, in another embodiment, R and R 1All are methyl (they being that carbonic ester is a dimethyl carbonate), in another embodiment, and R and R 1All are ethyl (that is, carbonic ester is a diethyl carbonate).
In one embodiment, acid-sensitive fluid composition of the present invention further comprises at least a solvent.This solvent can be any solvent that can be used for preparing photo-corrosion-resisting agent composition, or other nonpolar hydrocarbon solvents.Useful solvent comprises methyl proxitol acetate (PGMEA) ad lib, 3-methoxyl-3-methyl butanol, 2-heptanone (methyl amyl ketone), the glycol monomethyl methyl ether, ethylene glycol monomethyl ether, carbiphene, propylene glycol monomethyl ether (PGME), ethylene glycol monomethyl ether acetate, ethylene glycol monomethyl ether acetate, or the monohydroxy monocarboxylate, as hydroxy methyl acetate, hydroxyl ethyl acetate, the glycolic acid butyl ester, methoxy menthyl acetate, methoxyacetic acid ethyl ester, the methoxyacetic acid butyl ester, ethoxy acetate, ethoxy ethyl acetate, ethoxyethyl propionate, the 3-hydroxy methyl propionate, 3-hydracrylic acid ethyl ester, 3-methoxypropionic acid methyl esters, 3-methoxy propyl acetoacetic ester, the 2 hydroxy propanoic acid methyl esters, the 2 hydroxy propanoic acid ethyl ester, 2 hydroxy propanoic acid ethyl ester (ethyl lactate), 3-hydracrylic acid ethyl ester, the 2 hydroxy propanoic acid propyl ester, 2-ethoxy-propionic acid methyl esters, 2-methoxy propyl propyl propionate, cyclopentanone, cyclohexanone and their potpourri.In the middle of these, most preferred solvent is methyl proxitol acetate (PGMEA), methyl proxitol (PGME), cyclopentanone, cyclohexanone and 2 hydroxy propanoic acid ethyl ester (ethyl lactate).
In one embodiment, fluid composition comprises the solvent of 50-80wt% carbonic ester and 20-50wt%, based on the general assembly (TW) of fluid composition.In one embodiment, the ratio of carbonic ester and solvent is in 60: 40 to 80: 20 scope, and in another embodiment, this ratio is 65: 35 to 80: 20, in another embodiment, is 70: 30 to 80: 20, in a further embodiment, this ratio is 75: 25.
A kind of filter disc of the present invention (a) comprises the self-supporting fibre substrate that wherein is fixed with particle filtration aid and particle ion exchange resin; this ion exchange resin has about 2 to about 10 microns particle mean size, and wherein said particle filtration aid and ion-exchange resin particles are evenly distributed on the whole cross section of described matrix basically.The particle filtration aid of filter disc is preferably used acid elution.The acid that is used for acid elution is mineral acid preferably, the solution of example hydrochloric acid, formic acid, acetate, propionic acid, butyric acid, oxalic acid, succinic acid, sulfonic acid and nitric acid.This class filter disc is preferably at U.S. Patent number 6,103, the sort of described in 122, and can be at title Zeta Plus (Meriden, Conn. U.S.A.) are purchased from CUNOIncorporated under the 40Q.
The particle ion exchange resin that can use in above filter disc comprises Zeo-karb, anion exchange resins and their potpourri.The Zeo-karb that can use in the preparation of filter disc is not special restriction.The Zeo-karb that is fit to comprises sulfonated phenol-formaldehyde condensation products, sulfonated phenol-benzaldehyde condensation product, sulfonated phenylethylene-divinyl benzene copolymer, the polymkeric substance that contains sulfonic acid or hydroxy-acid group of sulfonation methacrylic acid-divinyl benzene copolymer and other type.Should be noted that, the general and H+ counter ion counterionsl gegenions of Zeo-karb, NH4+ counter ion counterionsl gegenions or alkaline metal, for example K+ and Na+ counter ion counterionsl gegenions provide together.Preferably, the Zeo-karb of this paper utilization has the hydrogen counter ion counterionsl gegenions.A kind of preferred particle particulate cation exchange resin is available from Purolite (Bala Cynwyd, Microlite PrCH Pa.).This is the sulfonated phenylethylene-divinyl benzene copolymer with H+ counter ion counterionsl gegenions.
Suitable anion exchange resins is well known in the art, and for example is disclosed in Samuelson, Ion Exchange Separations In Analytical Chemistry, JohnWiley ﹠amp; Sons, New York, 1963, among the Ch.2.The preferred anionic surfactants exchange resin is those resins with hydroxyl counter ion counterionsl gegenions, and wherein hydroxyl is incorporated in the photo-corrosion-resisting agent composition in exchange process.Here, the preferred anionic surfactants exchange resin is those resins with quaternary ammonium hydroxide cation exchange groups of chemical bonding, for example styrene diethylene benzene copoly mer that is replaced by tetramethyl ammonium hydroxide.The crosslinked polystyrene that the preferred anionic surfactants exchange resin is replaced by quaternary ammonium hydroxide is as at trade name AMBERLYST The ion exchange resin of selling and under DOW G51-OH, selling by Rohm andHaas Company under the A-26-OH by Dow ChemicalCompany.
Various types of particle filtration aids are arranged, they can be advantageously used in above filter disc, comprise zeyssatite, magnesium oxide, perlite, talcum, cataloid, polymer beads those as producing by emulsion or suspension polymerization, polystyrene for example, polyacrylate, poly-(vinyl acetate), tygon, (or as at Emulsions and Emulsion Technology, Lissant, Kenneth J., Marcel Dekker, this class material of described in 1974 other), activated charcoal, molecular sieve, clay etc.
Operable suitable self-supporting fibre substrate comprises polyacrylonitrile fibre in above filter disc, nylon fiber, and rayon fiber, polyvinyl chloride fibre, cellulose fibre, as wood pulp and cotton, and estron.
In one embodiment, filter disc (a) further comprises resin glue.The resin glue that is suitable for filter disc comprises the melamine formaldehyde (MF) colloid, as in U.S. patent Nos.4,007,113 and 4,007, those disclosed in 114, polyamide-polyamine epichlorohydrin resins is as in U.S. patent No.4,859, those disclosed in 340, with polyalkylene oxide as at U.S. patent No.4, those disclosed in 596,340.Polyamide-polyamine epichlorohydrin resins is preferred, and can buy, for example PolycupTM 1884,2002 or S2063 (Hercules), CascamideTM ResinpR-420 (Borden) and Nopcobond TM35 (Nopco).
In one embodiment, above filter disc has the average pore size of about 0.5-1.0 μ m.
Second kind of filter disc of the present invention (b) is the filter disc that comprises the self-supporting fibre substrate that wherein is fixed with particle filtration aid and resin glue, and this filter disc has the average pore size of 0.05-0.5 μ m, is 0.2 μ m in one embodiment.
The self-supporting fibre substrate can comprise and is selected from polyacrylonitrile fibre, nylon fiber, rayon fiber, polyvinyl chloride fibre, the fiber in the cellulose fiber peacekeeping estron.Preferably, self-supporting matrix is cellulose fiber substrate.Cellulose fibre preferably has approximately by comprising+400 to approximately+the non-refining cellulose pulp of the Canadian Standard Freeness (Canadian Standard Freeness) of 800ml. and having approximately+100 to the cellulose paper pulp mixture of the height refining cellulose pulp of the Canadian Standard Freeness of about-600ml derives, as at U.S. patent No.4, disclosed such in 606,824.
This filter disc does not preferably contain any ion exchange resin, and preferably at trade name ZetaPlus (Meriden, Conn. U.S.A.) are purchased, and are described in U.S. patent No.4, in 606,824 from CUNO Incorporated under 020 EC.
This method comprises allows the above-mentioned acid-sensitive fluid composition that contains carbonic ester pass through filter disc.This acid-sensitive fluid composition can pass through one of filter disc, or passes through two kinds of filter discs of any order.That is, acid-sensitive fluid composition can only pass through filter disc (a), only by filter disc (b), earlier by filter disc (a) and back by filter disc (b), or earlier by filter disc (b) and after pass through filter disc (a).
In one embodiment, acid-sensitive fluid composition of the present invention is being lower than 50/1000000000ths (50ppb) separately by having after filter disc ((a) and (b)) at least a, or is lower than 25ppb, or is lower than the concentration of sodium and the ferric ion of 10ppb.
In one embodiment, acid-sensitive fluid composition of the present invention is by having the concentration of the halide ion (as fluorine, chlorine, bromine, iodine) that is lower than 200ppb after filter disc ((a) and (b)) at least a.
In one embodiment, acid-sensitive fluid composition of the present invention is being lower than anionic concentration: NO below 200ppb at least a by having after filter disc ((a) and (b)) at least a 2-, NO 3-, PO 4 3-, SO 4 2-And HSO 4 -Metallic coating usually can be corroded because of these anionic existence, and usually uses the edge bead remover on metallic coating.
The acid-sensitive carbonic ester of the present invention is Undec advantage by filter disc the time.The use of other ion exchange technique has caused the decomposition of carbonic ester, and is undesirable.Carbonic ester decomposes and can monitor by the pure content (alcohol being decomposed to form by carbonic ester) and the increase of other decomposition product.
The present invention also provides the method that places lip-deep photo-corrosion-resisting agent composition film of handling, this method comprises allows photo-corrosion-resisting agent composition contact with fluid composition by method for preparing, presents in an amount at least sufficient to make the photo-corrosion-resisting agent composition that has basic homogeneous film thickness on this whole film surface.Like this, this fluid composition is edge bead remover (EBR).Therefore the present invention provides the method for producing EBR.
Following specific embodiment provides the detailed description of producing and utilize method for compositions of the present invention.Yet these embodiment have been used for anything but limiting the scope of the invention and should be considered to provide and implemented condition, parameter or the value that the present invention institute must special employing.Unless otherwise prescribed, all parts and percentage are by weight.
Embodiment
Embodiment 1
Two online filters that are connected in series are installed in 1 gallon of polypropylene containers.First filter is 47mm Zeta Plus (from CUNO Incorporated (Meriden, Conn. U.S.A.) obtain), back one is Zeta Plus to 40Q plate-like filter disc 020 EC plate-like filter disc (average pore size 0.2 μ m).To keep at room temperature by the following liquid of filtering system, and use the flow velocity of about 30 mm/min (ml/min) to allow liquid pass through this filtering system.Use nitrogen pressure, force liquid to pass through this filtering system.Filtration unit at first cleans with the washing fluid of the anhydrous 2-propyl alcohol of two parts of 500ml.Then by allowing 300ml electron level dimethyl carbonate wash by filtration unit.After this, allow the fluid composition of 75: 25 (weight) potpourris that belong to dimethyl carbonate and cyclopentanone of 450ml pass through filter device with the speed of 30ml/min.Regularly took out sample down, again by atomic adsorption spectroscopic methodology monitoring metallic ion level at 0,2,6,10 and 14 minute.The result provides in table 1." tester " is meant unfiltered fluid composition.
Table 1
Time (minute) Sodium (ppb) Potassium (ppb) Iron (ppb)
0 (contrast) 14 3 146
2 1 1 1
6 1 1 1
10 1 1 2
14 2 1 2
Sample is analyzed by vapor-phase chromatography (GC), does not show the increase of methyl alcohol (can exist if the decomposition of dimethyl carbonate takes place in expection) content or other decomposition product, illustrates that filter medium does not cause undesirable decomposition of dimethyl carbonate.
Embodiment 2
According to the operation identical with embodiment 1, the final fluid composition that different is by filtration unit is the identical dimethyl carbonate sample (potpourri that replaces dimethyl carbonate and cyclopentanone) by filtration unit in advance.Regularly took out sample down, again by atomic adsorption spectroscopic methodology monitoring metallic ion level at 0,2,6,10 and 16 minute.The result provides in table 2." tester " is meant unfiltered fluid composition.
Table 2
Time (minute) Sodium (ppb) Potassium (ppb) Iron (ppb) The % dimethyl carbonate 1
0 (contrast) 68 12 1 99.93
2 1 1 1 99.93
6 1 1 1 99.93
10 1 1 1 99.93
16 1 1 1 99.93
1 GC assay determination by sample.Percentage is meant the % area of GC curve.
Embodiment 3
According to the operation of embodiment 2, different is in beginning (tester or not filtered sample) and monitored chloride level after 10 minutes.Initial chloride level is 1.7ppm, and is below 200ppb after 10 minutes.
With reference to embodiment 1
At first analyze sodium, potassium and the iron of 10ml dimethyl carbonate sample, then by 0.2 micron (μ m) Teflon TMSyringe filter filters.The result provides in table 3." tester " is meant unfiltered dimethyl carbonate.
Table 3
Sample Sodium (ppb) Potassium (ppb) Iron (ppb)
Tester 12 12 233
The dimethyl carbonate that filters 12 10 229
These data show, use this TeflonTM filtrator not cause the decline of trace metal ion level.
With reference to embodiment 2
With the dried Ecodex of dimethyl carbonate (75g) with 2g TM202A (mixed bed cellulose anionic/cationic material is available from Graver Chemical Company) at room temperature mixed 2 hours, refiltered.The GC of filtering material the analysis showed that and formed 0.22% methyl alcohol, shows Ecodex TM202A has caused the part decomposition of dimethyl carbonate.
Above-mentioned each file is introduced for reference here comprehensively.
Except in an embodiment, or beyond the occasion that otherwise expressly provided, all quantity of prescribed material amount, reaction conditions (as temperature), molecular weight, carbon number etc. are construed as with word " approximately " and modify in this description.
Though explained the present invention, it should be understood that after having read this instructions its various modification are conspicuous to those technician in this area with regard to preferred embodiment.Therefore, much less, the present invention disclosed herein has comprised these modification in the appended claims scope.

Claims (22)

1, produce the method for acid-sensitive fluid composition, said method comprising the steps of:
Allow and contain useful formula ROC (=O) OR 1The acid-sensitive fluid composition of the carbonic ester of expression is at least a by following two kinds of filter discs, wherein R and R 1Independently be the alkyl of 1 to 10 carbon atom:
(a) comprise the filter disc of the self-supporting fibre substrate that wherein is fixed with particle filtration aid and particle ion exchange resin, described ion exchange resin has 2 to 10 microns particle mean size, and wherein said particle filtration aid and ion-exchange resin particles are evenly distributed on the whole cross section part of described matrix basically; And/or
(b) comprise the filter disc of the self-supporting fibre substrate that wherein is fixed with particle filtration aid and resin glue, described filter disc has 0.05 to 0.5 micron average pore size;
Thereby obtain acid-sensitive fluid composition.
2, the process of claim 1 wherein R and R 1Independently be methyl or ethyl.
3, the process of claim 1 wherein that acid-sensitive fluid composition further comprises at least a solvent.
4, the method for claim 3, wherein this solvent is to be selected from methyl proxitol acetate, methyl proxitol, cyclopentanone, at least a in cyclohexanone and the 2 hydroxy propanoic acid ethyl ester.
5, the method for claim 3, wherein R and R 1All be that methyl and solvent are cyclopentanone.
6, the method for claim 5, wherein this fluid composition comprises that 50 arrive the carbonic ester of 80wt% and 20 to 50wt% cyclopentanone, based on the general assembly (TW) of this fluid composition.
7, the method for claim 6, wherein the weight ratio of carbonic ester and cyclopentanone is in 60: 40 to 80: 20 scope.
8, the method for claim 7, wherein the weight ratio of carbonic ester and cyclopentanone is in 70: 30 to 80: 20 scope.
9, the method for claim 3, wherein R and R 1All be that ethyl and solvent are methyl proxitols.
10, the method for claim 9, wherein the weight ratio of carbonic ester and methyl proxitol is in 60: 40 to 80: 20 scope.
11, the process of claim 1 wherein fluid composition at first by filter disc (a), then by filter disc (b); Or wherein fluid composition passes through filter disc (a) then at first by filter disc (b).
12, the process of claim 1 wherein that filter disc (a) has 0.5 to 1.0 micron average pore size.
13, the process of claim 1 wherein that the ion exchange resin of filter disc (a) comprises Zeo-karb.
14, the method for claim 13, wherein the ion exchange resin of filter disc (a) comprises the potpourri of Zeo-karb and anion exchange resins.
15, the process of claim 1 wherein that filter disc (a) further comprises resin glue.
16, the process of claim 1 wherein that filter disc (a) and/or self-supporting fibre substrate (b) comprise is selected from polyacrylonitrile fibre, nylon fiber, rayon fiber, polyvinyl chloride fibre, the fiber in cellulose fibre and the estron.
17, the process of claim 1 wherein the particle filtration aid acid elution of filter disc (a).
18, the process of claim 1 wherein that filter disc (b) does not contain any ion exchange resin.
19, the process of claim 1 wherein by filter disc (a) and (b) at least a after fluid composition have the sodium that is lower than 50ppb separately and the concentration of ferric ion.
20, the method for claim 19, wherein by filter disc (a) and (b) at least a after fluid composition have the sodium that is lower than 25ppb separately and the concentration of ferric ion.
21, the process of claim 1 wherein by filter disc (a) and (b) at least a after fluid composition have following one or more anionic concentration: the NO that are lower than 200ppb 2 -, NO 3 -, PO 4 3-, SO 4 2-, HSO 4 -And halogen.
22, produce the method for acid-sensitive fluid composition, said method comprising the steps of:
Allow and contain useful formula ROC (=O) OR 1The acid-sensitive fluid composition of the carbonic ester of expression is at least a by following two kinds of filter discs, wherein R and R 1Independently be the alkyl of 1 to 10 carbon atom:
(a) comprise the filter disc of the self-supporting fibre substrate that wherein is fixed with particle filtration aid that acid elution crosses and particle ion exchange resin, described ion exchange resin has 2 to 10 microns particle mean size, and wherein said particle filtration aid and ion-exchange resin particles are evenly distributed on the whole cross section part of described matrix basically; With
(b) comprise the filter disc of the self-supporting cellulose fiber substrate that wherein is fixed with particle filtration aid and resin glue, described filter disc does not contain any ion exchange resin and has 0.05 to 0.5 micron average pore size; Thereby obtain acid-sensitive fluid composition.
CNB028080866A 2001-04-11 2002-03-19 Process for producing acid sensitive liquid composition containing a carbonate Expired - Fee Related CN1221864C (en)

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